HCID 12515637, compound → HCID 12515638, compound

HRID 1449061Notes

Reaction equation

HRID 1449061 reaction equation
[C:1]1([CH:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:8][N:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([C:16]3([OH:36])[CH2:21][CH2:20][N:19]([CH2:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:18][CH2:17]3)[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1>[C:1]1([CH:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH:11]([C:16]3([OH:36])[CH2:21][CH2:20][N:19]([CH2:22][CH:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:18][CH2:17]3)[CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 12515637HCID 12515637, compound

Product 1

HCID 12515638HCID 12515638, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.5 Parts by volume of 1.5 M solution of lithium perhydro-9b-boraphenallyhydride in tetrahydrofuran is added to a stirred, cold (-78° C.) solution of 0.65 part of 1-(2,2-diphenylethyl)-3-[1-(2,2-diphenylethyl)-4-hydroxypiperidin-4-yl]-4-piperidinone in 25 parts by volume of tetrahydrofuran under nitrogen atmosphere. The reaction is allowed to run for about 30 minutes and then it is quenched with the addition of 25 parts by volume of 10% ammonium chloride solution. Ethyl ether is added to the reaction mixture and it is allowed to warm to room temperature. After 2 hours the organic layer is separated and then extracted twice with 10% hydrochloric acid. The combined acid extracts are made alkaline with 50% sodium hydroxide and then extracted twice with ethyl ether. The organic fractions are combined, dried, and concentrated to yield yellow gum which crystallizes when triturated with ethyl ether to afford 1-(2,2-diphenylethyl)-3-[1-(2,2-diphenylethyl)-4-hydroxypiperidin-4-yl]-4 -piperidinol. This compound melts at about 174°-175° C. after recrystallization from absolute ethanol, and is represented by the following structural formula ##STR39##

Workup

  1. customit is quenched with the addition of 25 parts by volume of 10% ammonium chloride solution
  2. additionEthyl ether is added to the reaction mixture and it
  3. customAfter 2 hours the organic layer is separated
  4. extractionextracted twice with 10% hydrochloric acid
  5. extractionextracted twice with ethyl ether
  6. customdried
  7. concentrationconcentrated
  8. customto yield yellow gum which
  9. customcrystallizes when
  10. customtriturated with ethyl ether

Sources & evidence

ORD record
ord-a8597914724245949d5903707cde888b
Source dataset
uspto-grants-1980_02
Patent number
US04188485

Reaction notes

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